Triphenylphosphine → 3-[4-(Aminomethyl)-1,2,5-oxadiazol-3-yl]-4-(3-chloro-4-fluorophenyl)-1,2,4-oxadiazol-5(4H)-one

HRID 2097618Notes

Reaction equation

[N:1]([CH2:4][C:5]1[C:6]([C:10]2[N:14]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[C:17]([Cl:22])[CH:16]=3)[C:13](=[O:23])[O:12][N:11]=2)=[N:7][O:8][N:9]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.O>[NH2:1][CH2:4][C:5]1[C:6]([C:10]2[N:14]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[C:17]([Cl:22])[CH:16]=3)[C:13](=[O:23])[O:12][N:11]=2)=[N:7][O:8][N:9]=1

Participants

Conditions

Temperature: 0 °C

Procedure

3-[4-(Azidomethyl)-1,2,5-oxadiazol-3-yl]-4-(3-chloro-4-fluorophenyl)-1,2,4-oxadiazol-5(4H)-one (225 mg, 0.66 mmol) was dissolved in anhydrous THF (5.6 mL) and water (5.6 mL). The reaction was cooled to 0° C. followed by addition of triphenylphosphine (192 mg, 0.73 mmol). The reaction was allowed to warm to rt and was stirred overnight. The reaction was stripped to dryness, azeotroped with toluene and redissolved in MeOH. The crude residue was purified by preparative LCMS to yield the desired product (200 mg, 96%). MF═C11H7ClFN5O3; LCMS calculated for C11H8ClFN5O3(M+H)+: m/z=312.030.

Workup

temperatureto warm to rt
customazeotroped with toluene
dissolutionredissolved in MeOH
customThe crude residue was purified by preparative LCMS

Sources & evidence

ORD record: ord-45b2c719e15343469f0e0a49ae967d6a
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08450351B2

Reaction notes

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